NP-MRD: Showing NP-Card for (1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate (NP0222974)

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Record Information

Version

2.0

Created at

2022-09-06 00:56:39 UTC

Updated at

2022-09-06 00:56:39 UTC

NP-MRD ID

NP0222974

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate

Description

(1R,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-9-yl (2E,4E)-deca-2,4-dienoate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Based on a literature review very few articles have been published on (1R,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-9-yl (2E,4E)-deca-2,4-dienoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202562D          

 43 45  0  0  1  0            999 V2000
    3.5076    1.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4146    1.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    1.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6877   -0.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -0.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179   -1.3001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3682   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6782   -2.1094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4835   -2.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -2.6528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3086   -3.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -4.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2122   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6411   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3556   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0701   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7846   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4990   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4704   -2.5168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1270   -3.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -1.5777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6648   -1.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044    0.0408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4191    0.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766   -0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7369   -1.0343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1590   -1.9725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0262   -1.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272   -2.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185   -3.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4228   -2.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834   -2.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1047   -2.4027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6430   -3.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -4.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2091   -4.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2110   -4.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 32 31  1  1  0  0  0
  7 32  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END


  Mrv1652309062202562D          

 43 45  0  0  1  0            999 V2000
    3.5076    1.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4146    1.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    1.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6877   -0.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -0.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179   -1.3001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3682   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6782   -2.1094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4835   -2.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -2.6528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3086   -3.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -4.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2122   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6411   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3556   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0701   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7846   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4990   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4704   -2.5168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1270   -3.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -1.5777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6648   -1.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044    0.0408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4191    0.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766   -0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7369   -1.0343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1590   -1.9725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0262   -1.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272   -2.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185   -3.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4228   -2.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834   -2.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1047   -2.4027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6430   -3.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -4.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2091   -4.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2110   -4.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 32 31  1  1  0  0  0
  7 32  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222974

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C\C=C\C(=O)O[C@H]1[C@H](O)[C@@]23[C@@H](OC(C)=O)O[C@H](OC(C)=O)C2=C[C@H](O)C[C@H]3[C@](C)(CCC(=C)C=C)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O9/c1-8-10-11-12-13-14-15-16-28(38)42-29-22(4)33(7,18-17-21(3)9-2)27-20-25(37)19-26-31(40-23(5)35)43-32(41-24(6)36)34(26,27)30(29)39/h9,13-16,19,22,25,27,29-32,37,39H,2-3,8,10-12,17-18,20H2,1,4-7H3/b14-13+,16-15+/t22-,25+,27+,29-,30+,31+,32+,33-,34-/m1/s1

> <INCHI_KEY>
WGHDGSZCVSIZQE-MRXMUHBJSA-N

> <FORMULA>
C34H48O9

> <MOLECULAR_WEIGHT>
600.749

> <EXACT_MASS>
600.329833126

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
66.31111198996315

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[1,8a-c]furan-9-yl (2E,4E)-deca-2,4-dienoate

> <JCHEM_LOGP>
5.554362880666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.865210489571659

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.463419262301368

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8664961596440337

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
163.23610000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[1,8a-c]furan-9-yl (2E,4E)-deca-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       6.547   3.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.374   2.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.967   1.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.609   2.268   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.017  -0.047   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.747  -1.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.833  -2.427   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.421  -2.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.133  -3.938   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.636  -4.581   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.974  -4.952   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.443  -6.732   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.862  -7.551   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.862  -9.091   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.195  -6.781   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.529  -7.551   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.863  -6.781   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.196  -7.551   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.530  -6.781   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.864  -7.551   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.197  -6.781   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.531  -7.551   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.865  -6.781   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.878  -4.698   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.237  -6.027   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.217  -2.945   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.241  -2.449   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.540  -0.938   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.382   0.076   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.782   1.619   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.076  -0.420   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.376  -1.931   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.163  -3.682   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.782  -3.668   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.904  -4.776   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.514  -6.266   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.389  -4.369   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.276  -4.940   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.195  -4.485   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.200  -6.007   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.017  -7.640   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.257  -8.553   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -0.394  -8.257   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   32                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   11   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   32   39                                             
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    7   26                                                  
CONECT   33   27   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   39                                                       
CONECT   39   38   26   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1R,3R,5R,6AS,7S,8S,9R,10R,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6ah,7H,8H,9H,10H-naphtho[4,4a-c]furan-9-yl (2E,4E)-deca-2,4-dienoic acid	Generator

Chemical Formula

C₃₄H₄₈O₉

Average Mass

600.7490 Da

Monoisotopic Mass

600.32983 Da

IUPAC Name

(1R,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[1,8a-c]furan-9-yl (2E,4E)-deca-2,4-dienoate

Traditional Name

(1R,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[1,8a-c]furan-9-yl (2E,4E)-deca-2,4-dienoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C\C=C\C(=O)O[C@H]1[C@H](O)[C@@]23[C@@H](OC(C)=O)O[C@H](OC(C)=O)C2=C[C@H](O)C[C@H]3[C@](C)(CCC(=C)C=C)[C@@H]1C

InChI Identifier

InChI=1S/C34H48O9/c1-8-10-11-12-13-14-15-16-28(38)42-29-22(4)33(7,18-17-21(3)9-2)27-20-25(37)19-26-31(40-23(5)35)43-32(41-24(6)36)34(26,27)30(29)39/h9,13-16,19,22,25,27,29-32,37,39H,2-3,8,10-12,17-18,20H2,1,4-7H3/b14-13+,16-15+/t22-,25+,27+,29-,30+,31+,32+,33-,34-/m1/s1

InChI Key

WGHDGSZCVSIZQE-MRXMUHBJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Naphthofuran
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Cyclic alcohol
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.55	ChemAxon
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	163.24 m³·mol⁻¹	ChemAxon
Polarizability	66.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28944947

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162822774

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate (NP0222974)

MOL for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

3D MOL for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

3D SDF for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

3D-SDF for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

PDB for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

3D PDB for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

SMILES for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

INCHI for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

Structure for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)

3D Structure for NP0222974 ((1r,3r,5r,6as,7s,8s,9r,10r,10as)-1,3-bis(acetyloxy)-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-9-yl (2e,4e)-deca-2,4-dienoate)